Caroline and the Painting
by notPrinceHamlet
Summary: In an alternative timeline where Caroline and Richard begin dating in the winter of 1997, Caroline goes to see Titanic and wants Richard to paint her naked.
1. Chapter 1

[Scene: Early 1998. A movie theater. Caroline and Annie are seeing _Titanic_.]

ANNIE: Why didn't Richard come with you, again?

CAROLINE: He absolutely refuses to see this movie. Apparently he thinks it's a 'stale love story template set on a boat filled with aristocratic British produced by corporate America for the purpose of profit without regard for artistic value.'

ANNIE: Wow.

CAROLINE: I know. He repeated it ten times to make sure I got it right.

ANNIE: You'd think he'd enjoy something that involves lots of people drowning.

[Scene: The apartment building hall.]

CAROLINE: I got an idea tonight, but I'm not sure about it.

ANNIE: Don't tell me you're thinking about going on a cruise.

CAROLINE: No, it's about Richard and me.

ANNIE: Well if Richard went on a cruise I bet plenty of people would be going overboard.

CAROLINE: You know we haven't slept together yet.

ANNIE: I figured that as you never told me you did.

CAROLINE: Hey I didn't tell you about Del for almost… 2 days.

ANNIE: You've been going out for almost three months.

CAROLINE: I know, but I've had so many one night stands and relationships that have ended badly and I really want it to work out with Richard so I've been taking it slow.

ANNIE: Well maybe you should do it before Manhattan sinks into the Atlantic. If you think you're ready, then go for it!

CAROLINE: Not quite.

ANNIE: Then what's your big idea?

CAROLINE: This is embarrassing to say. Let's go into my apartment.

[Enter Caroline's apartment.]

RICHARD: Hey honey!

[They kiss]

RICHARD: I got all of the panels ready. Your syndicate called and said that your next strip is due a day early. Tuesday at 9pm, instead of Wednesday.

CAROLINE: What why?

RICHARD: Something about a new digital computer thing. Y2K. Computer taking over the world. Who knows? I need to get going. I'm going to meet David Miller.

CAROLINE: David Miller, the owner of that museum on the upper east side?

RICHARD: He's not the owner, just the curator.

CAROLINE: Well all that matters is that he likes your art.

RICHARD: Not likely. This guy is the harshest critic on the East coast. Painters are said to end up at the Louvre or flipping burgers on his opinion.

ANNIE: Don't worry Richie. With your work, I'm sure you'll end up flipping burgers at the Louvre.

RICHARD: Hopefully, if in your next Broadway show you play a cow.

[Exit Richard]

ANNIE: What a fun little man.

CAROLINE: You know you don't help when he's on edge and uptight like that.

ANNIE: He colors in cartoons for dirt money. The fast food thing might be a step up for him.

CAROLINE: Yes, but he gets to spend all day with me. That's reward enough.

[Caroline opens her door and looks out]

ANNIE: What are you doing?

CAROLINE: Checking to make sure he's gone.

ANNIE: Oh, that's right. You still haven't told me of your dirty little X-rated fantasy.

CAROLINE: No, this is PG13.

ANNIE: Must you ruin everything with your Midwest restraints?

CAROLINE: That's all very relative. In Wisconsin what I'm thinking might…

ANNIE: Will you get to your fantasy already?

CAROLINE: I'm a little embarrassed to say considering all of the dirty stuff I've told you over the years…

ANNIE: What? Is it about someone other than Richard?

CAROLINE: Oh no, it's not that.

ANNIE: Is it about something Richard might actually enjoy doing? Because if it is, you should be scared.

CAROLINE: Yes and it does scare me. But something tells me it's a good idea.

ANNIE: I could tell you if it's a good idea or not if you let me know what the idea is.

[Caroline pauses for a moment]

CAROLINE: I want Richard to paint me naked, the way Jack drew Rose naked in the movie.

[Annie stands silent and in shock for several seconds]

CAROLINE: Annie, are you ok?

ANNIE: [stuttering] You know technically, if you were to measure it, like a scientist, on a scale, that's not as dirty as even the most gentle and loving kind of sex, but it still sounds pretty shocking.

CAROLINE: I know, but I think it would be fun.

ANNIE: What are you going to do with it when he's done?

CAROLINE: I'm going to see if they'll put it up in Times Square. What do you think? Lock it in the vault.


	2. Chapter 2

[Scene: Caroline's apartment.]

CAROLINE: How did David Miller like your paintings?

RICHARD: Quite a bit. I think I'm making real progress as an artist.

CAROLINE: Oh?

RICHARD: Yes, it took him forty-five seconds to tell me how horrible they were. I can still remember the days when it only took most people ten seconds. Those were the days.

CAROLINE: Well you'll always be my favorite artist.

RICHARD: By the way, I got the supplies to paint the picture of Salty. Though to be honest there are more creative things I could do. Maybe tinting her red for Valentines Day…

CAROLINE: Trying for some kind of surrealism again?

RICHARD: I meant dumping the bottle right on her.

CAROLINE: What an artist. You'd be willing to waste a bottle of paint just to spite an animal.

RICHARD: Well what's 'waste' is a matter of opinion.

CAROLINE: Richard, forget about painting Salty.

RICHARD: Geez, will you lighten up. I'll paint your damn cat.

CAROLINE: [Voiceover in her head] I wonder if he'll appreciate the pun in that.

[She puts her arms around his neck]

CAROLINE: Honey I want you to paint me.

RICHARD: Holding the cat? Ok, but you're going to have to sit still with her for a long time. Where are you planning on putting this painting anyway because if it's on that wall…

CAROLINE: I want you paint me naked.

[Richard passes out. Caroline catches him.]

CAROLINE: Well if he ever needs surgery again at least I know how to save him some money on anesthesia.

[She puts him on the couch. Enter Del]

Del: [looking at Richard] I've told him he needs to try some energy bars. Who takes a nap at three in the afternoon?

CAROLINE: If he were awake he'd have some snappy comeback. Speaking of which I need you out of here before he wakes up.

DEL: Ok, ok. I just came by to show you the prototype for the new Caroline in the City T-shirt line.

CAROLINE: Oh my God, you got me my own T-shirt line?

DEL: Wait until you see this.

[He holds a shirt up]

CAROLINE: Um, Del, is that all there is?

DEL: Well…

CAROLINE: So your idea is to have Caroline in the City shirts without midriffs.

DEL: It's a new market but…

CAROLINE: Del did you attend one class of business school or did you spend it all in bed?

DEL: Well not to brag but, ok fine, it's a bad idea. Sorry to bring it up.

CAROLINE: No, no, I'm glad you're thinking of new things. I'm just a little stressed because I had my own little idea and Richard passed out after hearing it.

DEL: Wow, you never made me pass out the entire time we were dating.

CAROLINE: Not with anything I said, at least.

DEL: Yeah, yeah. I'll see you later.

[Exit Del.]


	3. Chapter 3

[Scene: Caroline's apartment. She washes his forehead with a wet washcloth. Richard wakes up.]

RICHARD: I don't remember falling asleep.

CAROLINE: You didn't exactly fall asleep.

RICHARD: Normally I don't open my eyes and get off a couch in a haze without falling asleep first. The last thing I remember was you wanted me to paint Salty and then… oh my God…

CAROLINE: Richard don't pass out again…

RICHARD: No, no, I won't. Do you really want me to…

CAROLINE: Yes, Richard. I thought you'd look forward to it, but passing out?

RICHARD: [stuttering] Um, oh, um, alright, just for the record this was _your_ idea.

CAROLINE: Yeah.

RICHARD: Your idea out of nowhere which I had nothing to do with.

CAROLINE: Yes, Richard. I know what we're about to do.

RICHARD: I'm going to have to go back to the art store. I don't have enough of the colors I'll need for this.

CAROLINE: Ok, I'll be here when you get back.

RICHARD: [stuttering] I thought I was going to paint Salty, that's why I don't have the right paints to do it.

CAROLINE: Yes. Go, before it gets dark.

RICHARD: I should probably buy a few new paintbrushes, too. I'd hate to mess this up…

CAROLINE: Richard, clam down. Go get what you need and you'll be relaxed by the time you get back.

RICHARD: Relax? You don't think I'm relaxed?

CAROLINE: You're very hard to read, but no.

RICHARD: No, no. I'm fine with your idea, your idea…

CAROLINE: Richard what's wrong?

RICHARD: Ok Caroline. Since fate loves to play little games with me and you'll probably end up finding this out somehow, someway, I have to tell you this now.

CAROLINE: Richard I know you've painted women naked before so don't tell me you don't know how to do it. Remember Donna?

RICHARD: I did the same thing for Julia.

CAROLINE: Julia? Oh, Julia! Your unquestioned love in Italy.

RICHARD: Yes. I did a nude of her while we were in Venice.

CAROLINE: Is there anything in Italy you didn't do?

RICHARD: Yeah, sell a painting. Maybe I should have stuck with naked women.

CAROLINE: I don't mind what you did with her. This is my idea. This is you and me. Now forget about her and go get what you need.

RICHARD: How much wine do you have left?

CAROLINE: About half a bottle but it might be gone by the time you get back.

[Exit Richard]

[Scene: The hallway outside Caroline's apartment]

RICHARD: [voiceover in his mind] She wants me to paint her naked, just like Julia did. There's no doubt about it now, Richard. She's the new Julia. Your new sincere amore.

[Enter Annie from her apartment]

ANNIE: Richard, what's with the back pressed against the wall and the heavy breathing? Is there 75% off sale on black clothes at the GAP?

RICHARD: Shouldn't you be taking off 75% of your clothes in preparation for going out with some loser?

ANNIE: Ah, let met guess, Caroline just told you about her little fantasy.

RICHARD: What, she told you about that?

ANNIE: Yes, she has to run everything by me first. It's a new rule since what happened with Joe.

RICHARD: Eight million people in New York and you're the best proofreader she could find?

ANNIE: And you for her boyfriend. I guess she just doesn't like to travel far searching.

RICHARD: Yes, I'm sure that's why she left Wisconsin. Speaking of traveling I have to get to the store.

ANNIE: What for?

RICHARD: Paint.

ANNIE: Ah. You might want to pick up a few more things while you're there. Maybe some condoms and body oil…

RICHARD: Why? What?

ANNIE: I think she might want you to do more than just paint tonight…

RICHARD: Oh come on Annie.

ANNIE: No, no. Listen, do you think you're going to be staring at her all night like that without wanting to…

RICHARD: [Irritated] No, that is not going to happen. I'm not going to risk anything going wrong by jumping the gun with this. I'm a professional artist. I know how to control myself. I've done with before with other women.

ANNIE: None of those other women were Caroline.

RICHARD: When it comes time for Caroline and I to do what you're talking about…

ANNIE: That time's tonight, Richie.

RICHARD: I've been stupid enough to listen to people like you before and it's brought me nothing but trouble.

ANNIE: Richard, she's my best friend, and she isn't getting any younger. I don't want anything to go wrong between the two of you. I want Caroline to be happy.

RICHARD: I need to get going.

[Richard enters the elevator]


	4. Chapter 4

[Scene: Caroline's apartment. Enter Richard. Caroline is standing in her robe.]

CAROLINE: You're back.

RICHARD: [nervously] I see you have the curtains pulled.

CAROLINE: Get everything ready.

RICHARD: You have everything set up. I just need to open these canisters and I'm ready.

[She walks to the door and locks it and turns the lights down]

CAROLINE: What are you thinking right now, Richard?

RICHARD: Just how drunk I'm going to have to get in order to do this without messing it up.

[He pulls a bottle of wine out of the bag, opens it, and drinks it]

RICHARD: That should do.

[Caroline lights some candles]

CAROLINE: You're always on the defensive, Richard. Tonight, just let your guard down.

[Caroline takes off her robe and kisses Richard]

RICHARD: [hesitating] Caroline, this is going to be the most difficult and pleasurous thing I've ever done.

CAROLINE: Richard you're the most difficult and pleasurous person I've ever met.

[He begins painting her]

RICHARD: So did you ever get your Christmas pictures from Wisconsin developed?

CAROLINE: Oh yeah, it was a really great time. But it was so much colder than I remember. I've been thinking of taking trips there in the summer instead when it will be nice.

RICHARD: Is your brother still dating that law student?

CAROLINE: No, they broke it off.

RICHARD: Oh that's too bad. He could have had someone to defend him if his work ever got too sloppy.

CAROLINE: No, Chris hasn't lost a patient yet.

RICHARD: Are we still going to that thing next month?

CAROLINE: Oh, yeah. Del got tickets to _Cyrano de Bergerac_ for Christmas but he has no interest in going so he said I could have them.

RICHARD: Oh, good then. It's really a great play.

CAROLINE: I thought that it would be. Richard, when you were in Paris, what did you do?

RICHARD: Paris? Oh, in the summer of '96?

CAROLINE: Yeah.

RICHARD: Well after arriving at the Paris airport I found the cheapest apartment in the city and spent almost three months trying to sell my paintings on the Seine.

CAROLINE: And no one in the whole city would buy anything?

RICHARD: I sold a few, but only for a few thousand dollars altogether. I guess I was lucky to get that.

CAROLINE: Did you do any painting there?

RICHARD: Of course.

CAROLINE: Did you think of me when you were painting?

RICHARD: Well, yeah. I thought of you everyday.

[He continued painting her nude, trying to stay on focus and talk to her at the same time]

CAROLINE: Did you do any paintings of me there?

RICHARD: Now that you mention it, at least three.

CAROLINE: What were they about?

RICHARD: Well there was _Caroline In Love With Someone Else_, _Caroline Engaged To Someone Else_, and _Caroline Marries Someone Else_.

CAROLINE: That's so sweet. What ever happened to them?

RICHARD: I was going to sell a couple of them to this old French guy but he disappeared after making an offer. At first I thought he just ran off but it turns out he fell into the Seine.

CAROLINE: Not that I'm glad he was hurt, but I'm glad you had to come back to New York.

[Scene: Caroline's apartment. Later. Richard has finished painting.]

RICHARD: Ok, just let that dry. I hope you like it.

CAROLINE: I'm sure I'll love it. Richard, next week has to be our first time.

RICHARD: When?

CAROLINE: Saturday night. I'll find a hotel somewhere.

RICHARD: Aren't you going to put your clothes back on?

CAROLINE: Not yet.

**The End. **


End file.
